Potassium Carbonate → 1,3-dimethyl-5-(4-methylpiperazin-1-yl)-1H-pyrazole-4-carbaldehyde

HRID 2387139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2387139
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(P(N(C)C)(N(C)C)=O)C.O>[CH3:7][N:6]1[C:2]([N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)=[C:3]([CH:9]=[O:10])[C:4]([CH3:8])=[N:5]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

Produkt 1

HCID 337871101,3-dimethyl-5-(4-methylpiperazin-1-yl)-1H-pyrazole-4-carbaldehydeAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
122.5 °C

Versuchsvorschrift

To a solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (25.4 g, 0.16 mol) in HMPA (25 mL) and water (25 mL) was added 1-methylpiperazine (40 g, 0.4 mol, 2.5 equiv), and the mixture was heated at 120-125° C. for 25 h. When the reaction was completed, the reaction mixture was poured into water (500 mL), and potassium carbonate was added to make the medium strongly alkaline. The mixture was extracted with dichloromethane (5×100 mL). The combined organic extracts were washed twice with water and dried with sodium sulfate, and the solvent evaporated. The residue was purified chromatographically on silica gel with gradient elution from dichloromethane to methanol, affording 10.2 g (29%) of the title product. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, DMSO-d6): δ 2.23 (s, 3H), 2.26 (s, 3H), 2.44 (m, 4H), 3.16 (m, 4H), 3.59 (s, 3H), 9.88 (s, 1H). LC-MS (API-ES) calcd for C11H18N4O: 222.15, found (M+H+): 223.1 m/z.

Aufarbeitung

  1. additionwas added
  2. extractionThe mixture was extracted with dichloromethane (5×100 mL)
  3. washThe combined organic extracts were washed twice with water
  4. dry with materialdried with sodium sulfate
  5. customthe solvent evaporated
  6. customThe residue was purified chromatographically on silica gel with gradient elution from dichloromethane to methanol

Quellen und Nachweise

ORD-Eintrag
ord-74fb6ee4eb5b41caa1d8618b59be914d
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268835B2

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